By Baila Sebrow


I grew up in a chassidishe home. My parents were very careful to take care of the looks of their daughters, but not their sons. For example, my sisters got contact lenses, while my brothers and I always wore thick ugly glasses. My sisters have beautiful teeth because they got braces. My brothers and I never got braces, and my teeth are the worst in the whole family.

My life was also hard because I didn’t want to stay in yeshiva and learn. I went to work for someone my parents know, and, baruch Hashem, I now have my own business. Because I didn’t stay in learning I couldn’t make a good shidduch, but now that I have a successful business, shidduchim are starting to come my way.

The first thing I did when I had my own money was get contact lenses so that I don’t have to be embarrassed by the way I look in ugly glasses. The other problem is harder to fix. I need braces because my teeth are so crooked, and I have a bad bite, so the dentist said I might also need surgery. The other problem is that my teeth look rotted because they are so stained.

Baruch Hashem, I can afford to fix my teeth, but it could take a few years. In the meantime, I don’t know what to do about shidduchim. Should I wait until I look good? I want to get married, and I don’t want to wait so long.

There is a nice girl who works for me. I know that she likes me, because a shadchante my mother knows wanted to redd her to me. Also, I see the way she looks at me when she talks to me. I don’t know if I should go out with her or not. She is very nice, but I also want to know other girls, too, and how can I do that with the problem I have?

Also, if I meet somebody I like, should I tell her what I really looked like before? I am worried that she won’t want to marry me, because she will be scared that our children could look like me. Right now, I look ugly.


Your letter is very sad. If I were to read your letter backwards, I believe that your problem is not entirely about your thick glasses or your teeth. You really believe that you are an unattractive person. Regardless of the condition of your teeth, you are being very hard on yourself. After you have all your dental needs taken care of, do you think that you will then start to see yourself as a good-looking man? Do you think that your perception of your appearance will improve?

One of the main reasons I question your perception of yourself is because you stated that a girl who works for you is interested in you. She surely feels some sort of attraction towards you to have a shadchante contact your mother to redd the shidduch. She makes it very clear that she would like to get to know you outside of work. She obviously does not think that you are ugly! Not only that, you acknowledge that she looks at you in a way that makes you think she likes you.

While you may need a bit of cosmetic dental work, perhaps even for your health, you come across as having an unhealthy view of yourself. It is not uncommon for people to look in the mirror and feel that the reflection staring back at them is unattractive. The problem with that viewpoint is that it usually ends up affecting every other area in life.

And I wonder what happened in your earlier years when you felt that you couldn’t get any good shidduchim suggested to you because you left yeshiva.

It is true that in chassidishe circles, a boy who learns full-time in yeshiva will be suggested to a girl who seeks that type. There are cases where learning is not for every boy and he goes out to work. Shidduchim for such a boy can be challenging if his parents want him to marry a girl who seeks a learning boy. Otherwise, there are other types of shidduchim for him, which begs the question:  What held you back then? Did your parents not approve of the type of girl who would be OK with a boy who doesn’t stay in yeshiva? Or was it your thick glasses and your teeth that held you back? Is it because you now have a successful business so you feel at least a little bit better about yourself that shidduchim are coming your way?

My first concern is about your well-being and future happiness. It’s important to take care of yourself and your appearance for the right reasons. But what is really going on here? You need to know what you are setting yourself up for. From what you are describing about your teeth, it sounds like you might be headed towards serious dental surgery. You might be right that it could take a few years to get everything corrected. But there is still no guarantee that it would work 100 percent to your liking.

Here is what I am concerned about. If you were confident about yourself, and you still don’t see the success you hoped for after you have all that work done, then you would probably deal with it one way or another. But with the way you view yourself, what will you do if the results do not turn out as you imagined? This is not a blunder in the color choice of your socks or shirt, where you could just change it.

There’s another issue. You ask whether you should disclose your dental work to a girl because you are worried that if she finds out about your natural appearance, she will assume that the children she will have with you will look like that and she may decide not to marry you.

That’s a very interesting point, and I will share with you a situation I once had with a young lady. She was dating a guy, and a so-called “do-gooder” decided to share with him that the girl he was dating had a nose job. This individual even went so far as to dig up old school photos of the girl. To make a long story short, that shidduch almost fell apart because he felt misled. It took a lot to salvage that shidduch, but in the end, it all worked out. They got married and had adorable children!

Had you not brought up the issue about informing a girl you get involved with about how you looked before your cosmetic work, I wouldn’t bring it up. Corrective or cosmetic surgery sounds like an attractive option for those who are not happy with certain features. Although it is important to educate yourself about the risks and results before you jump into it, there is no need to tell anyone anything about it. However, it sounds like you are worried that it could backfire, so if it has to backfire, then it’s better that she knows before you get serious with one another.

It is more common in women, but it happens to guys, too. They keep changing things about themselves, whether through something simple like dieting or a radical method like surgery, and they don’t know when to stop and feel “shidduch-ready.” Bear in mind that a person can change various physical aspects only to discover that their bashert is someone who may appreciate their original appearance.

Another point I would like to address is that you mention you want to know other girls, too, even though there is somebody who is interested in you now. This is a serious matter. There are cases of people who go through either cosmetic surgery or extreme weight loss while married to somebody, and afterwards they wonder what it would be like for them if they venture into the world looking better than before. There are cases where divorces have happened for this reason alone.

I don’t know how old you are, but irrespective of that, you are new to the shidduch world because you are feeling comfortable being there now. For the purpose of preventing future regrets, it would not be a bad idea for you to have a few shidduchim redd to you so that you get to know other girls. You might need to get that out of your system, and, who knows—that might even help you build a strong relationship with the girl who likes you as you are now. You may end up appreciating her that much more!

Baila Sebrow is president of Neshoma Advocates, communications and recruitment liaison for Sovri-Beth Israel, executive director of Teach Our Children, and a shadchanis and shidduch consultant. She can be reached at Questions and comments for the Dating Forum can be submitted to


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